Sodium hydride → Ethyl 5-[(phenylmethyl)oxy]-1-(2,2,2-trifluoroethyl)-1H-indole-2-carboxylate

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

A solution of 5-benzyloxyindole-2-carboxylic acid ethyl ester (purchased at Biosynth, ref B2000, 2.26 g, 1.0 eq.) in dimethylformamide (15 mL) was added to a suspension of sodium hydride (60% dispersion in oil, 367 mg, 1.2 eq.) in dimethylformamide. The reaction mixture was stirred 50 min at 70° C. 2,2,2-Trifluoroethyltrifluoromethanesulfonate (3.0 g, 1.7 eq.) was added and the reaction mixture was stirred overnight at 70° C. The reaction mixture was partitioned between ethyl acetate and water. The aqueous layer was extracted with ethyl acetate and the combined organic fractions were washed with water and brine, evaporated to dryness and purified on silica eluting with 9:1 cyclohexane/ethyl acetate to yield 1.9 g (66%) of the desired product as light yellow solid. MS (m/e): 378.5 (MH+, 100%).

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